The Buccaneer

3 BR
2 Baths
Sleeps 9


Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. This charming and fun home has a four-season patio, with adjustable plexiglass windows, overlooking the fenced-in backyard and full entertainment room in the basement, complete with foosball, an arcade and a theater room.

This home's full kitchen, dining area, family room, bedroom with Queen bed and full bath are on the main floor. The kitchen is fully-stocked with cookware, stainless steel appliances and a chef's butcher block built into the countertop. The custom dining room table is built in to allow up to 8 guests to gather and enjoy a family meal. Head out to the 4-seasons room/screened-in porch and private backyard.

The 2nd bedroom, located upstairs, has a bunk bed with a Full bed over 2 Twin beds. The 3rd bedroom, also located on the 2nd floor, has a King bed.

The home is just a short walk through a quiet neighborhood to Capital SUP on Back Creek, where paddle boards and kayaks are available for rent. Looking for a fun adventure on the water? You will be conveniently located within walking distance to Ellen Moyer Park, Annapolis Maritime Museum and Bert Jabin Yacht Yard. Or, take a water taxi into Annapolis! Just 2 blocks away at the waterfront of King James Landing, you can hire a water taxi.


Main Floor Bedroom:

-Queen Bed

-Full bathroom in the hall with shower/bath combo

King Bedroom

-2nd Floor

-Full bath in the hall with shower/bath combo

Upstairs family guest room

-Full bed over Two Twins bunk bed

-Full bath in the hall with shower/bath combo

Family Room

Queen sleeper sofa


-Large screened-in patio overlooking the big private backyard

-Built-in kitchen dining table seats 6-8

-High Speed Internet and WiFi

-Coffee maker with starter pack of coffee/creamers

-BBQ gas grill (propane included)

-Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service

-Parking for 2-3 cars in driveway

-Full-sized washer & dryer

-Private fenced-in backyard

-Dogs allowed with $150 non-refundable fee paid prior to checkin

-Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions.


Property Distance to:

-Downtown Annapolis – 2.5 miles (10 mins)

-U.S. Naval Academy – 3 miles (10 mins)

-Washington, DC – 33 miles

-Baltimore - 34 miles


* Amenity pack with starter coffees, sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going

* All beds are made for you with freshly-laundered sheets & towels in the baths.

House Rules

Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents. Please respect the neighbors and neighborhood. No parties. Quiet neighborhood hours are 9pm-8am!

Check-in time: 4:00 pm

Check-out time: 11:00 am

1008 Hyde Park Dr Annapolis, MD 21403
Registration Number: STR24-145379

Sleeping Arrangements

Main Floor Bedroom Queen
Upstairs King King
Upstairs Bunk Room Bunk Combo
Family Room Sofa Queen

Bathroom Configuration

Main Floor: Combo Tub Shower, Toilet
Upstairs Hall Bath: Combo Tub Shower, Toilet

Property Rules

Check In: After 4pm
Check Out: Before 11am
Smoking: Not Allowed


Air Conditioning
Arcade game
BBQ Grill
Bath Towels
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Cooking basics
Corn Hole
Covered Patio
Dining room
Enhanced Cleaning
Full Kitchen
Hair Dryer
High Chair
Ice Maker
Internet Access
Iron and Board
Living room
Outdoor games
Parking Available
Pets Considered
Private Backyard
Private entrance
Screened Patio
Self Check-In
Smoke Detector
Smoke alarms
Travel crib
Washing Machine
body wash
hot water
portable crib


Frequently Asked Questions


Tenant is at least 25 years old and will be an occupant of the unit The Buccaneer. Should any unauthorized persons occupy or use the Premises, Tenant shall vacate the premises immediately without any refund.


Balance is due 30 days prior to arrival date and includes a refundable damage deposit. The balance is due on _BalanceDueDate_. Payment may be made by major credit card. 


Cancellations must occur at least 30 days prior to arrival date, or WILL BE CHARGED THE FULL AMOUNT. If cancellation occurs 30 days or more prior to arrival date all monies will be refunded with the exception of a $100.00 administrative fee.


No BBQ grills of any kind are permitted in the unit. No open flames permitted in the unit.


If you wish to bring your dog, you will need to pay the $150 non-refundable pet deposit per pet prior to arrival.  If you bring an unathorized pet on to the property, you will be asked to vacate immediately with no refund of rent or damage deposit. Homeowner and Agent assume no responsibility for any illness or injury that may occur to pets or humans while on the premises. Homeowner and Agent assume no responsibility for the behavior of the pet(s); that responsibility is the Tenant owner.


Any reservation obtained under false pretense will be subject to forfeiture of reservation deposit, damage deposit, and/or balance of rental payment.


There is no daily maid service. Linens and towels are included and not to be taken from the unit. There is a $_CleaningFee_ one time cleaning fee.


No compensation will be given for temporary outage of electricity, gas, water or cable. 


Your damage deposit will be forfeited and you will incur an additional charge for cleaning and deodorizing if any evidence of smoking is found.


Owner or owner's agents may enter the premises: in case of an emergency; to make any necessary or agreed upon repairs, alterations, or improvements; supply necessary or agreed upon services or show the premises to prospective purchasers, renters or contractors.  24 hours notice of Owners intent to enter will be given (except in the case of an emergency).


  1. Tenant agrees to leave the premises and its contents in the same condition, neat and tidy, as Tenant found the premises to be upon move-in, normal wear and tear expected. Please leave all used towels on the floors of the bathrooms and beds linens should all be left on each bed for housekeeping.
  2. All dishes are to be washed and all garbage removed from the premises and placed in outside receptacles. If these items are not completed, the guest will be charged an additional cleaning fee. 
  3. The maximum number of occupants shall not exceed 9 people, not including a child in a crib.
  4. Furnishings are not to be removed from the premises for use outside or in other properties.
  5. No Smoking.
  6. Reservations are not made by or for a minor, defined as any person under the age of 25.
  7. Tenant and any guest of Tenant shall obey all laws of the state of Maryland, as well as local laws, at all times while they are on the premises. Failure to abide by the laws of Maryland or the above rules may cause tenant to be asked to vacate the premises and forfeit all rents and security/damage deposits.
  8. All noise must be brought inside by 10pm. Failure to do so could result in a $500 fine.


Tenant and all other occupants will be required to vacate the premises and forfeit the rental fee and security deposit for: Occupancy exceeding the sleeping capacity of 9 people, using the premises for illegal activity, causing damage to the premises rented or to any of the neighboring properties and any other acts which interferes with neighbors' right to quiet enjoyment of their premises.


iTrip or the Owner, does not assume any liability for loss, damage or injury to persons or their personal property. Neither does owner accept any liability for any inconveniences, damage, loss or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, electricity or plumbing, as well as due to weather conditions, natural disasters, acts of God, or other reasons beyond its control.


Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos.


Great trip!
5/5 stars
We have loved exploring Annapolis and DC with our family. The house has all the things we need and the added bonus of being kid friendly! We are loving it, thank you!
- Katie

Thank you for allowing us to host your stay Katie & we welcome you back anytime! Melissa~iTripAnnapolis

- Manager Response

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Contact Manager

Phone (410) 571-4076